NPASS drugs

Drug Information

Drug ID:	NPD5157
Drug Name:	Lobeline
Molecular Formula:	C22H27NO2
Canonical SMILES:	O[C@H](c1ccccc1)C[C@@H]1CCC[C@@H](N1C)CC(=O)c1ccccc1
Standard InCHI:	"InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1"
Standard InCHIKey:	MXYUKLILVYORSK-HBMCJLEFSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5157

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	113618
0.1-0.2	96050
0.2-0.3	1927
0.3-0.4	119
0.4-0.5	13
0.5-0.6	2
0.6-0.7	4
0.7-0.8	3
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similar Natural Products

High Similarity: Tc>=0.85; Intermediate Similarity: 0.7 <= Tc < 0.85; Remote Similarity: 0.5 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC254822
High Similarity	1.0	NPC285394
High Similarity	1.0	NPC611697
High Similarity	0.8936	NPC181939
Intermediate Similarity	0.7381	NPC292758
Intermediate Similarity	0.7381	NPC11541
Intermediate Similarity	0.7381	NPC65855
Remote Similarity	0.6875	NPC566859
Remote Similarity	0.66	NPC255205
Remote Similarity	0.6471	NPC558933
Remote Similarity	0.6458	NPC538771
Remote Similarity	0.5098	NPC501220
Remote Similarity	0.5098	NPC511483

Drug Structure

NPD5157 OpenBabel08211706322D 26 28 0 0 1 0 0 0 0 0999 V2000 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 15 1 1 0 0 0 19 23 1 0 0 0 0 20 16 1 1 0 0 0 20 23 1 0 0 0 0 21 15 1 6 0 0 0 21 24 1 0 0 0 0 22 25 2 0 0 0 0 24 26 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank	DB05137
ChEMBL	CHEMBL122270
IUPHAR/BPS
PharmaGKB
KEGG Drug	D02364
PubChem CID	0
ChEBI	48723
CAS Number	90-69-7

Drug Properties

Molecular Weight	337.2
ALogP	-1.877
MLogP	3.55
XLogP	6.146
HDA	3
HBD	1
Rotatable Bonds	8
TPSA	40.54
RO5 Violation	1